I do think that you sometimes have to push kids and others to come out their comfort zone though. Otherwise they may never grow. My son needed a firm hand and support doing things first time in the parks. He'd have done nothing without that. He was a fair bit older at 7 and hated doing things he couldnt see what was to come so he'd go on Barnstormer etc but not the dark rides. Think I got a bit frustrated with him when he wouldn't go on the Jimmy Neutron ride at Universal and he gave in, loved it and went on several times in a row. But same problems next ride. Now I know he's in the autistic spectrum it makes sense but at the time it took all I had not to snap at him because there were 6 other people on that holiday wanting to do things together. And I knew him, knew he was fine and what he needed. The youngest was J$ age, in and out of a stroller, happy playing in the splash zones and honestly it never crossed anyone's mind to take her on a coaster!! Jenn has projected so many anxieties on $J, trained him to be scared and anxious. Then they get annoyed when he shows these anxieties and it prevents them doing things. Poor boy
Being timid is a good thing, it's a survival instinct and more than once has saved a child from doing something stupid their parent wanted them to do.
Two years old is a ridiculous age to be tossing on a thrill ride. There is NO THRILL in it for a 2 year old. Let's not talk about how asinine it is to keep stats for how many rolly coasters they've been on before even being potty trained or has full 20/20 vision developed.
Toddlers crave putting their hands on things, running, or maybe even sitting in a tea cup and spinning. They l-o-v-e being spun around by their parent's arms. The MK splash pad is wonderful, Jackson would adore that. Why not let him zip about giggling and having a blast there? If they fear him getting wet, just bring a swimsuit, Tee and footwear that he can change into. At this rate he may never be allowed to enjoy the Magic Kingdom the way it's intended for small children. Everything sized down for him or wet or featuring other child-centric focus is an inconvenience for Tim and Jenn won't do it on her own with him.
SOME DAY, I'd love to see Jenn get out of her sorry head full of "what do I get out of this" and hop in the car (or call a Lyft) taking Jackson someplace fun on her own, no need to get Timmy to join in or even his approval. Just go do it and ignore all other responsibilities that day. Do you think she can? No, she's stuck in a shell where she cannot be apart from her electronics or even breathe fresh air without her security blanket there to do literally everything for her (I'm talking either Tim or Stanny). It's not just Jackson who's missing the thrill in life, it's Jenn too. She needs to step out on her own, out of her comfort zone.